Natürel Zeytinyağında Etil Alkol ve Etil Ester Oluşumu ile Tespit Yöntemleri

Yıl 2021, , 343 - 352, 19.10.2021

Ümmühan Tibet Pelin Günç Ergönül Fahri Yemişçioğlu

https://doi.org/10.24323/akademik-gida.1011230

Öz

Natürel sızma zeytinyağı, dünyada olduğu gibi ülkemizde de en çok aranılan ve ilgi duyulan gıdalardan birisidir. Bu sebeple de en fazla hile yapılan yağlar arasında yer almaktadır. Natürel sızma zeytinyağında “kolon yağı” olarak ifade edilen işlem görmüş zeytinyağı karışımını tespit etmek için yağ asidi etil esterlerin (FAEE) analizinin yapılması gerekmektedir. Ancak etil esterler sadece kolon yağı tağşişi ile yükselmeyip fermentatif bozulma olduğunda, depolama sürecinde ya da diğer kalite kriterlerinde düşme olduğunda limit üzerine çıkabilmektedir. Son yıllarda, etil esterlerin oluşum mekanizmaları incelenerek tarladan sofraya etil ester seviyesinin hangi koşullarda yükseldiğini araştıran birçok makale yayınlanmıştır. Bu çalışmada, etil esterlerin oluşum mekanizması, etil alkolün zeytinyağında esterleşmesini tetikleyen faktörler irdelenmiş ve tespit yöntemleri üstünde durulmuştur.

Anahtar Kelimeler

Alkil esterler, Etil ester, Etil alkol, Natürel sızma zeytinyağı

Formation of Ethyl Alcohol and Ethyl Esters in Virgin Olive Oil and Their Detection Methods

Öz

Extra virgin olive oil is one of the most demanded foods in our country as well as in the world. It is among oils, which is mostly adulterated due to its high demand. For this reason, it is one of the most adulterated oils. Analysis of fatty acid ethyl esters must be carried out in order to detect the processed olive oil mixtures, which is expressed as "mild deodorization oil" in extra virgin olive oil. Ethyl esters not only can reach the limit by mild deodorization of olive oil, but also can rise with fermentative deterioration or with esterify during storage. In recent years, many articles have been published, studying the conditions under which ethyl esters rise from field to table, by examining the formation mechanism of ethyl esters. In this review article, the formation mechanism of ethyl esters and the factors triggering the esterification of ethyl alcohol in olive oil were presented.

Anahtar Kelimeler

Alkyl esters, Ethyl ester, Ethyl alcohol, Extra virgin olive oil

Kaynakça

• [1] Huang, C.L., Sumpio, B.E. (2007). Olive oil the Mediterranean diet and cardiovascular health. Journa of the American College of Surgeons, September, 207(3):407-416.
• [2] Perez-Jimenez, F., Ruano. J., Perez-Martinez, P., Lopez-Segura, F., Lopez-Miranda, J. (2007). The influence of olive oil on human health; not a question of fat alone. Molecular Nutrition, Food Research, 51(10), 1199-1208.
• [3] Covas, M.I. (2007). Olive oil and the cardiuvascular system. Pharmacological Research Rev 55, 175-186.
• [4] Covas, M.I., Konstantinidou, V., Fito, M. (2009). Olive oil and cardiovascular health. Journal of Cardiovasc Pharmacol, 54, 477-482.
• [5] Lanzon, A., Albi, T., Cert, A., Gracian, J. (1994). The hydrocarbon fraction of virgin olive oil and changes resulting from refining. Journal of the American Oil Chemists, 71, 285–291.
• [6] Perona J.S., Botham K.M. (2013) Olive Oil as a Functional Food: Nutritional and Health Benefits. In: Aparicio R., Harwood J. (eds) Handbook of Olive Oil. Springer, Boston, MA.
• [7] Garcia, J.M., Seller, S., Perez-Camino, M.C. (1996). Influence of fruit ripening on olive oil quality. Journal of Agricultural and Food Chemistry, 44, 11, 3516–3520.
• [8] Gomez-Coca, R.B., Moreda, W., Perez-Camino, M.C. (2012). Fatty acid alkyl esters presence in olive oil vs. organoleptic assessment. Food Chemistry, 135(3), 1205-1209.
• [9] Morales M.T., Aparicio-Ruiz R., Aparicio R. (2013) Chromatographic Methodologies: Compounds for Olive Oil Odor Issues. In: Aparicio R., Harwood J. (eds) Handbook of Olive Oil. Springer, Boston, MA.
• [10] TGK (2010). Türk Gıda Kodeksi Zeytinyağı ve Prina Yağı Tebliği (Tebliğ No 2010/35), Resmi Gazete, Ankara.
• [11] IOC (2011). International Olive Council Trade Standard Applying to Olive Oils and Olive Pomace Oils. COI/T.15/NC No 3/Rev. 6, Madrid, Spain.
• [12] Bendini, A., Cerretani, L., Salvador, M.D., Fregapane, G., Lercker, G. (2009). Stability of the sensory quality of virgin olive oil during storage: an overview. Italian Journal of Food Science, 21(4), 389-406.
• [13] Biedermann, M., Bongartz, A., Mariani, C., Grob, K. (2008). Fatty acid methyl and ethyl esters as well as wax esters for evaluating the quality of olive oils. European Food Research Technology, 228(1), 65-74.
• [14] Gómez-Coca, R.B., Fernandes, G.D., Pérez-Camino, M.del C., Moreda, W. (2016) Fatty acid ethyl esters (FAEE) in extra virgin olive oil: A case study of a quality parameter. Food Science and Technology, 66, 378–383.
• [15] Anonymous (2007). Official Journal of the European Union, L 299/115.
• [16] Aparicio-Ruiz, R., Romero, I., García-González, D.L., Oliver-Pozo, C., Aparicio, R. (2017). Soft-deodorization of virgin olive oil: Study of the changes of quality and chemical composition. Food Chemistry, 220, 42–50.
• [17] Grob, K., Biedermann, M., Bronz, M., Schmid, J.P. (1994). Recegnition of mild deodorization of edible oils by the loss of volatile components. Zeitschrift für Lebensmittel-Untersuchung und Forschung, 199,191-194.
• [18] Mariani, C., Venturini, S., Gasparoli, A., Tagliabue, S., Bondioli, P. (2000). Considerazoni preliminary relative agli oli lampanti deodorati. Rivista Italiana delle Sostanze Grasse, 77, 49-59.
• [19] Di Serio, M.G., Giansante, L., Di Loreto, G., Faberi, A., Ricchetti, L., Di Giacinto, L. (2017). Ethyl esters versus fermentative organoleptic defects in virgin olive oil. Food Chemistry, 219, 33–39.
• [20] García-Vico, L., Belaj, A., León, L., Rosa, R. de la, Sanz, C., Pérez, A.G. (2018). A survey of ethanol content in virgin olive oil. Food Control, 91, 248–253.
• [21] Beltran, G., Bejaoui, M.A., Jimenez, A., Sanchez-Ortiz, A. (2015). Ethanol in Olive Fruit. Changes during ripening. Journal of Agricultural and Food Chemistry, 63(22), 5309–5312.
• [22] Masella, M., Guerrini, L., Angeloni, G., Zanoni, B., Parenti, A. (2019). Ethanol from olive paste during malaxation, exploratory experiments. European Journal of Lipid Science and Technology, 121(1), 1800238.
• [23] Boudebouz, A., Agusti, R., Ricard, B., Montserrat, M. (2019). Effect of agronomic and technological factors on the formation of ethyl esters in virgin olive oil in Catalonia. Universitat Rovira I Virgili (URV)PhD student Annual Seminar 2019.
• [24] Köseoğlu, O., Sevim, D., Kadiroğlu, P. (2019). Effects of filtration on the quality properties of extra virgin olive oils during storage. Journal of the American Oil Chemists' Society, 96(3), 291-301.
• [25] Luna, G., Morales, M.T, Aparicio, R., (2006). Characterization of 39 varietal virgin olive oils by their volatile compositions. Food Chemistry, 98(2):243-252.
• [26] Garcia-Vico, L., Belaj, L., Leon, L., De la Rosa, R., Sanz, C., Perez, A.G. (2018). A survey of ethanol content in virgin olive oil. Postprint of Food Control, 91, 248-253.
• [27] Moyano, E., Encinas-Villarejo, S., López-Ráez, J.A., Redondo-Nevado, J., Blanco-Portales, R., Bellido, M.L., Sanz, C., Caballero, J.L., Muñoz-Blanco, J. (2004). Comparative study between two strawberry pyruvate decarboxylase genes along fruit development and ripening, post-harvest and stress conditions. Plant Science, 166, 835-845.
• [28] Tadege, M., Dupuis, I., Kuhlemeier, C. (1999). Ethanolic fermentation: new functions for an 342 old pathway. Trends in Plant Science, 8, 320-325.
• [29] Conte, L., Mariani, C., Gallina Toschi, T., Tagliabue, S. (2014). Alkyl esters and related 277 compounds in virgin olive oils: their evolution over time. Rivista Italiana Delle Sostanze 278 Grasse, 91, 21-29.
• [30] Salas, J.J., Sanchez, J. (1997). Biogenesis of alcohols present in the aroma of virgin olive oil. Physiology, Biochemistry and Molecular Biology of Plant Lipids, 328–330. [31] Perez-Camino, M.C., Moreda, W., Cert, A. (2002). Determination of Esters of fatty acids with low molecular weight alcohols in olive oils. Journal of Agricultural and Food Chemistry, 50(16), 4721-5.
• [32] Gómez-Coca, R.B., Moreda, W., Pérez-Camino, M.C. (2012). Fatty acid alkyl esters presence in olive oil vs. organoleptic assessment. Food Chemistry, 135(3), 1205–1209.
• [33] International Olive Council Chemist Meeting Report 10.09. (2015) Annex 5.a.1.
• [34] Jabeur, Zribi A, Abdelhedi, R., Bouaziz, M. (2015). Effect of olive storage conditions on Chemlali olive oil quality and the effective role of fatty acids alkyl esters in checking olive oils authenticity. Food Chemistry, 169, 289-296.
• [35] Mariani, C., Bellan, G. (2008). Individuazione di oli di qualità inferiore negli oli di oliva extra vergini. Rivista Italiana Delle Sostanze Grasse, 1, 3-20.
• [36] Alcala, S., Ocana, M.T., Cardenas, J.R., Miguel, A.M., Vilar, J., Espinda, F., Moya, M. (2017). Alkyl esters content and other quality parameters in oil mill. A response surface methodology study. Lipid Science European Journal, 119(1), 1600026.
• [37] Perez-Camino M. Cert A., Romero Segura, A. (2008). Alkyl esters of fatty acids a useful tool to detect soft deodorized olive oils. Journal of Agricultural and Food Chemistry, 56 (15)6740-6744.
• [38] Di Loreto, G., Giansante, L., Alfei, B., Di Giacinto, L. (2014). Alchil esteri ed altri indicatori per la tutela della qualita e della genuinita degli oli extra vergini Italiani. Rivista Italiana Sostanze Grasse, 91, 35-45.
• [39] Gómez-Coca, R.B., Fernandes, G.D., Pérez-Camino, M. del C., Moreda, W. (2016). Fatty acid ethyl esters (FAEE) in extra virgin olive oil: A case study of a quality parameter. Food Science and Technology, 66, 378–383.
• [40] IOC (2016). International Olive Council Electronic Working Group on Fatty Acid Ethyl Esters (FAEEs) in extra virgin olive oils (EVOO-Final Report 2016).
• [41] Mariani, C., Fedeli, E. (1986). Detection of extraction olive oils in pressure ones. Rivista Italiana Delle Sostanze Grasse, 63, 3-17.
• [42] TGK (2017). Türk Gıda Kodeksi Zeytinyağı ve Prina Yağı Tebliği (Tebliğ No: 2017/26), Resmi Gazete (Tarih: 17.09.2017, Sayı: 30183), Ankara.
• [43] EC Commission Regulation (EEC) (2011). No. 61/2011 of 24 January 2011 amending Regulation No. 2568/91 on the characteristics of olive oil and olive pomace oil and on the relevant methods of analysis. Official Journal of the European Communities, L 23, 1–14.
• [44] IOC (2016). International Olive Council Trade Standard COI/T.15/NC No 3/ Rev.11, Madrid, Spain.
• [45] TGK (2014). Türk Gıda Kodeksi Zeytinyağı ve Prina Yağı Analiz Metotları Tebliği (Tebliğ No: 2014/53), Resmi Gazete (Tarih: 20.11.2014, Sayı: 29181), Ankara.
• [46] IOC (2017). International Olive Council, Determination of the Content of Waxes, Fatty Acid Methyl Esters and Fatty Acid Ethyl Esters by Capillary Gas Chromatography COI/T.20TDoc.28/Rev.2, Madrid, Spain.
• [47] International Olive Council Electronic Working Group for Revision of Codex Trade Standard-Ethyl Esters 20042020-ENK.
• [48] Beltran, G., Sanchez, R., Sanchez-Ortiz, A., Aguilera, M.P., Bejaoui, M.A., Jimenez, A. (2016). How “ground-picked” olive fruits affect virgin olive oil ethanol content, ethyl esters and quality. Journal of the Science of Food and Agriculture, 96(11), 3801–3806.